A good way to test if your beaming is working from the device to the Empeg is to try to beam the playlist to a non-Empeg device (Palm, PocketPC, PC) that can recieve OBEX objects via IrDA. The beam should come over as an OBEX object file called palantir_insert.txt or such. That would verify that the PocketPC is actually beaming something over, and the problem might lie with the Empire setup on the Empeg.

Another way to check is to point a digital camera at the IrDA port of the PocketPC while beaming and see if there are any IR signals being sent by looking at the digicam's LCD.